Isolation of notoamide S and enantiomeric 6-epi-stephacidin A from the fungus Aspergillus amoenus: biogenetic implications.

Isolation of notoamide S and enantiomeric 6-epi-stephacidin A from the fungus Aspergillus amoenus: biogenetic implications.
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DOI:
10.1021/ol5037198
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发表时间:
2015-02-06
期刊:
影响因子:
5.2
通讯作者:
Tsukamoto S
Tsukamoto S
中科院分区:
化学1区
文献类型:
--
作者:
Kato H;Nakahara T;Sugimoto K;Matsuo K;Kagiyama I;Frisvad JC;Sherman DH;Williams RM;Tsukamoto S

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诺托酰胺S被认为是曲霉特征代谢物千金藤素A、诺托酰胺B和杂环菌胺B的关键生物合成中间体,但尚未分离到。报道了诺托酰胺S和富含(−)异构体的6-表-千金藤素A对映体混合物的分离。(+)-versicolide B的存在表明该真菌只具有将(+)-6-epi-stephacidin A转化为(+)-versicolide B的氧化酶,而不是(−)-6-epi-stephacidin A。
Notoamide S has been hypothesized to be a key biosynthetic intermediate for characteristic metabolites, stephacidin A, notoamide B, and versicolamide B, in Aspergillus sp., but has not yet been isolated. The isolation of notoamide S and an enantiomeric mixture of 6-epi-stephacidin A enriched with the (−)-isomer from A. amoenus is reported. The presence of (+)-versicolamide B suggests that the fungus possesses only the oxidase, which converts (+)-6-epi-stephacidin A into (+)-versicolamide B, but not for (−)-6-epi-stephacidin A.